Photoreaction of arenecarbothioamides with 2-vinylfuran analogues. The formation of tetracyclic indoles and 2,3-diaryl-2-pyrrolin-5-ones

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 10, 1998, Pages 1522-1526

  Oda, Kazuaki ^a   Tsujita, Hisao ^a   Sakai, Masayuki ^a   Machida, Minoru ^a  

^a HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

2 vinylfuran analogue; Arenecarbothioamide; Intermolecular photoreaction; Photochemistry; Pyrrolin 5 one; Tetracyclic indole

Indexed keywords

ACRYLIC ACID DERIVATIVE; BENZENE; ETHYLENE; FURAN DERIVATIVE; INDOLE DERIVATIVE; PYRROLINE DERIVATIVE; THIOAMIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0031772857     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1522     Document Type: Article

References (23)

1. a) Dedicated to Dr. Yuichi Kanaoka, Professor Emeritus, Hokkaido University, on the occasion of his 70th birthday;
2. b) Photochemistry of the Nitrogen-Thiocarbonyl Systems, Part 31, Part 30: Oda K., Sakai M., Machida M., Chem. Pharm. Bull., 45, 584-589 (1997).
3. Houlihan W. J., Saxton J. E.,"The Chemistry of Heterocyclic Compounds," Vol. 25, ed. by Weissberger A., Taylor E. C., John Wiley & Sons, New York, Part 1, 2; 1972, part 3; 1979, part 4; 1983.
4. Moskal J., van Leusen A. M., J. Org. Chem., 51, 4131-4139 (1986).
5. Moskal J., von Stralen R., Postma D., van Leusen A. M., Tetrahedron Lett., 27, 2173-2176 (1986).
6. Jones G. B., Mathews J. E., Banner K., Heterocycles, 38, 1221-1224 (1994).
7. Oda K., Tsujita H., Sakai M., Machida M., Heterocycles, 42, 121-124 (1996).
8. Padwa A., Mazzu K. U., J. Org. Chem., 43, 381-387 (1978).
9. Tsuge O., Kanemasa S., Yorozu K., Bull. Chem. Soc. Jpn., 59, 1809-1824 (1986).
10. Oda K., Machida M., Chem. Pharm. Bull., 41, 1229-1301 (1993).
11. Oda K., Machida M., J. Chem. Soc., Chem. Commun., 1993, 437-438.
12. Oda K., Machida M., J. Chem. Soc., Chem. Commun., 1994, 1477-1478.
13. Oda K., Tsujita H., Ohno K., Machida M., J. Chem. Soc., Perkin Trans. 1, 1995, 2931-2935.
14. Oda K., Hiratsuka R., Machida M., Heterocycles, 43, 463-470 (1996).
15. Oda K., Sakai M., Tsujita H., Machida M., Synth. Commun., 27, 1183-1189 (1997).
16. Laarhoven W. H., "Organic Photochemistry," Vol. 10, ed. by Padwa A., Marcel Dekker Inc., New York, 1990, pp. 163-308.
17. Irie M., Miyatake O., Uchida K., Eriguchi T., J. Am. Chem. Soc., 116, 9894-9900 (1994).
18. Hahama Y., Imoto M., Imai M., Kogyo Kagaku Zasshi, 45, 1059-1064 (1942).
19. Leuck, G. L., Cejka L., "Organic Syntheses," Coll. Vol. I, ed. by Gilman H., John Wiley and Sons, Inc., New York, 1956, pp. 283-284.
20. Povazanec P., Piklerova A., Zb. Pr. Chemickotechnol. Fac., 1978, 1975-1976 [Chem. Abstr., 90, 137589 (1979)].
21. Povazanec P., Piklerova A., Zb. Pr. Chemickotechnol. Fac., 1978, 1975-1976 [Chem. Abstr., 90, 137589 (1979)].
22. Matsuno K., Han K., Bull. Chem. Soc. Jpn., 12, 155-163 (1937).
23. Patterson J. M., "Organic Syntheses," Coll. Vol. V, ed. by Baumgarten H. E., John Wiley and Sons, Inc., New York, 1973, pp. 585-586.